(Z)-3-(3-fluorophenyl)-N-methyl-3-(2-tolyl)-2-propenamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(3-fluorophenyl)-N-methyl-3-(2-tolyl)-2-propenamide
• 英文别名: (Z)-3-(3-fluorophenyl)-N-methyl-3-(2-methylphenyl)prop-2-enamide
• 化学式: C₁₇H₁₆FNO
• 分子量: 269.319
• InChiKey: BPSFRKQMYWMWKD-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间氟碘苯 、 N-methyl-3-(2-tolyl)propiolamide 在 甲酸 、 二乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以68%的产率得到(Z)-3-(3-fluorophenyl)-N-methyl-3-(2-tolyl)-2-propenamide
  参考文献：
  名称：

  Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides

  摘要：

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.

  DOI：

  10.1021/jo980235h

文献信息

• PROCESS OF PREPARING SUBSTITUTED ACRYLAMIDES
  申请人：ELI LILLY AND COMPANY

  公开号：EP0944581A1

  公开（公告）日：1999-09-29
• EP0944581A4
  申请人：——

  公开号：EP0944581A4

  公开（公告）日：2004-09-08
• [EN] PROCESS OF PREPARING SUBSTITUTED ACRYLAMIDES<br/>[FR] PROCEDE DE PREPARATION D'ACRYLAMIDES SUBSTITUES
  申请人：ELI LILLY AND COMPANY

  公开号：WO1998022429A1

  公开（公告）日：1998-05-28

  (EN) The present invention relates to a process for preparing acrylamides; wherein, a propiolamide is reacted with an activated aromatic ring to yield a wide variety of acrylamides.(FR) La présente invention concerne un procédé de préparation d'acrylamides, dans lequel on met en réaction un propiolamide avec un noyau aromatique activé pour obtenir une grande variété d'acrylamides.
• Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides
  作者：Lynne A. Hay、Thomas M. Koenig、Francis O. Ginah、James D. Copp、David Mitchell

  DOI：10.1021/jo980235h

  日期：1998.7.1

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.